UV filter decomposition. A study of reactions of 4-(2-aminophenyl)-4-oxocrotonic acid with amino acids and antioxidants present in the human lens

UV filter decomposition. A study of reactions of 4-(2-aminophenyl)-4-oxocrotonic acid with amino acids and antioxidants present in the human lens Full article

Journal

Experimental Eye Research
ISSN: 0014-4835 , E-ISSN: 1096-0007

Output data

Year: 2007, Volume: 85, Number: 2, Pages: 242-249 Pages count : 8 DOI: 10.1016/j.exer.2007.04.008

Tags

kynurenine; UV filter compounds; cataract; deamination; lens protein modification

Authors

Kopylova Lyudmila V. ¹ , Snytnikova Olga A. ^1,2 , Chernyak Elena I. ³ , Morozov Sergey V. ³ , Tsentalovich Yuri P. ¹

Affiliations

1	(Данные Web of science) Int Tomog Ctr, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk State Univ, Novosibirsk 630090, Russia
3	(Данные Web of science) Novosibirsk Inst Organ Chem, Novosibirsk 630090, Russia

Deamination of UV filters, such as kynurenine (KN), in the human lens results in protein modification. Thermal reactions of the product of kynurenine deamination, 4-(2-aminophenyl)-4-oxocrotonic acid (CKA), with amino acids (histidine, lysine, methionine, tryptophan, tyrosine, cysteine) and antioxidants (ascorbate, NADH, glutathione reduced) were studied. The rate constants of the reactions under physiological conditions were measured. The rate constants of CKA addition to cysteine k(Cys) = 36 +/- 4 M-1 s(-1) and to glutathione k(GSH) = 2.1 +/- 0.2 M-1 s(-1) are 4-5 orders of magnitude higher than the rate constants of CKA reactions with the other amino acids and antioxidants. The Arrhenius parameters for k(Cys) and k(GSH) were determined: A(GSH) = (1.8 +/- 0.7) x 10(5) M-1 s(-1), E-GSH = 29.2 +/- 5.6 kJ mol(-1) A(Cys) = (2.7 +/- 0.9) x 10(8) M-1 s(-1), E-Cys = 40.4 +/- 5.7 kJ mol(-1). The large difference in frequency factors for k(Cys) and k(GSH) is attributed to steric hindrance, peculiar to the bulky GSH molecule. (c) 2007 Elsevier Ltd. All rights reserved.

Kopylova L.V. , Snytnikova O.A. , Chernyak E.I. , Morozov S.V. , Tsentalovich Y.P.
UV filter decomposition. A study of reactions of 4-(2-aminophenyl)-4-oxocrotonic acid with amino acids and antioxidants present in the human lens
Experimental Eye Research. 2007. V.85. N2. P.242-249. DOI: 10.1016/j.exer.2007.04.008 WOS Scopus РИНЦ

Published print:

Aug 1, 2007

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